Senior Product Designer, Client Management

📍 Job Overview

Job Title: Senior Product Designer, Client Management

Company: Headway

Location: New York, NY, United States

Job Type: FULL_TIME

Category: Product Design / UX/UI (with a strong GTM operational impact)

Date Posted: 2026-08-04

Experience Level: 5-10 years

Remote Status: Remote (within the United States)

🚀 Role Summary

• Own the end-to-end design of critical provider-facing client management tools, including calendar, scheduling, and messaging interfaces, directly impacting provider efficiency and patient access to care.

• Leverage AI-first design methodologies and tools (e.g., Claude, Cursor, MagicPatterns) to rapidly prototype, iterate, and deliver user-centered solutions.

• Drive the identification and resolution of complex, state-heavy usability challenges within provider workflows, ensuring a seamless and trustworthy user experience.

• Contribute to the evolution and application of the company's internal design system (Helix) by developing reusable scheduling and messaging patterns.

• Collaborate closely with Product Management, Engineering, and Data teams to translate user insights and business objectives into impactful design solutions.

📝 Enhancement Note: While this role is in Product Design, its focus on core provider workflows (scheduling, messaging, calendar management) has significant implications for Go-To-Market (GTM) operations and revenue enablement. Efficient provider tools directly translate to better patient acquisition, retention, and overall platform scalability, which are key GTM objectives. The "Client Management" aspect refers to the providers' clients (patients), not sales clients, but the operational impact on provider efficiency is paramount.

📈 Primary Responsibilities

• Lead the design strategy and execution for the Calendar and Scheduling features, ensuring accuracy and usability around availability, booking, rescheduling, time zones, and conflict resolution.

• Design and refine the Provider-Patient Messaging experience, including handling attachments and optimizing the notification and reminder systems to improve communication efficiency.

• Systematically identify and prioritize high-impact usability "papercuts" within Electronic Health Record (EHR)-like functionalities, directly addressing provider feedback to enhance daily workflows.

• Ensure design coherence and consistency between scheduling/messaging tools and the broader client management surfaces, such as client lists and profiles, in close partnership with Product Managers.

• Conduct user research, alongside the dedicated research team, to gather qualitative insights from providers, and translate these insights into actionable design improvements and new feature development.

• Elevate the visual and interaction design craft for scheduling and messaging, contributing new patterns and components to the Helix design system.

• Proactively use AI tools for rapid prototyping, code-based iteration, and to stay involved throughout the product lifecycle, from concept to post-launch analysis.

• Partner effectively with Product Managers, Engineers, and Data Analysts to build alignment, articulate design rationale, and drive project momentum.

📝 Enhancement Note: The emphasis on "EHR-craft papercuts" and "systems-minded craft to complex, state-heavy problems" indicates a need for a designer who can not only create aesthetically pleasing interfaces but also deeply understand and optimize intricate operational workflows that directly impact user productivity and error reduction. This requires a strong understanding of how design decisions influence operational efficiency.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's degree in Design, Human-Computer Interaction, or a related field is often preferred for senior-level product design roles. Equivalent practical experience will also be considered.

Experience: 5+ years of dedicated product design experience, with a proven track record of working on complex, workflow-heavy product surfaces that require meticulous attention to detail and state management.

Required Skills:

• Product Design Expertise: Demonstrated ability to own and drive the design of significant product features from concept to launch.

• Systems Thinking: Capacity to dissect complex, multi-state problems and synthesize them into coherent, user-friendly experiences.

• Exceptional Craftsmanship: High standards for visual design, interaction design, and a keen eye for detail, particularly in managing edge cases and states.

• AI Prototyping & Workflow: Proficiency and active use of AI tools (e.g., Claude Code, Cursor, MagicPatterns) as a core part of the design workflow.

• Cross-functional Collaboration: Proven ability to build strong partnerships and drive alignment with Product Management, Engineering, and Data teams.

• Data-Informed Decision Making: Skill in leveraging both qualitative (user research) and quantitative (data analytics) insights to inform design strategies.

• Design Systems Contribution: Experience in contributing to or extending design systems, creating reusable patterns for broader application.

Preferred Skills:

• Experience designing for SaaS platforms, particularly within healthcare or FinTech where complex workflows and data integrity are critical.

• Familiarity with EHR systems or similar complex workflow software.

• Experience with Google Calendar OAuth integrations and managing related complexities.

• Understanding of how to design for asynchronous communication and notification systems.

• Strong UI design skills with a portfolio showcasing polished interfaces.

📝 Enhancement Note: The explicit mention of AI tools like Claude, Cursor, and MagicPatterns as a core part of the workflow suggests that candidates who can demonstrate experience or a strong aptitude for integrating AI into their design process will have a significant advantage. This is a forward-thinking requirement that aligns with modern product development practices and efficiency gains.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Complex Workflow Case Studies: Showcase 2-3 detailed case studies focusing on complex, multi-state workflow problems you've solved, particularly in areas like scheduling, task management, or communication platforms.

• AI Integration Examples: Include examples or descriptions of how you've used AI tools in your design process (e.g., for rapid prototyping, code generation assistance, or research synthesis).

• Design System Contributions: Demonstrate your ability to create or extend design systems, showing examples of reusable components or patterns you've developed, especially for scheduling or messaging.

• Data-Informed Design Rationale: Clearly articulate how you've used both qualitative and quantitative data to inform your design decisions and measure impact within your case studies.

• Cross-functional Collaboration Artifacts: If possible, include examples of how you've collaborated with PM, Eng, and Data (e.g., shared documents, process flows, or joint presentations).

Process Documentation:

• Problem Definition & Research: Detail your approach to understanding user problems, including research methodologies and how you synthesized findings into actionable insights for complex workflow challenges.

• Solution Ideation & Prototyping: Showcase your process for generating design solutions, emphasizing the use of AI tools for rapid iteration and the development of detailed prototypes for complex states and edge cases.

• Impact Measurement & Iteration: Explain how you measure the success of your designs, focusing on metrics related to efficiency, task completion, error reduction, and user satisfaction within operational contexts.

📝 Enhancement Note: For a role focused on complex workflows and AI integration, the portfolio needs to go beyond static UI mockups. It should highlight the designer's ability to think systemically, use modern tools effectively, and demonstrate measurable impact on user efficiency and operational outcomes. The ability to present a coherent narrative around problem-solving, AI-assisted ideation, and data-driven iteration will be key.

💵 Compensation & Benefits

Salary Range: $180,000 - $225,000 annually. This range is based on the provided information and reflects a Senior Product Designer role in a high-cost-of-living area like New York City, with consideration for the company's Series D funding and established market presence.

Benefits:

• Equity Compensation: Meaningful ownership opportunities through equity grants.

• Comprehensive Health Coverage: Medical, Dental, and Vision insurance plans.

• Financial Wellness: Health Savings Account (HSA), Flexible Spending Account (FSA), and 401K retirement plan.

• Remote Work Support: Work-from-Home Stipend to enhance home office setup.

• Mental Health Support: Therapy Reimbursement and Employee Assistance Program (EAP).

• Family Support: 16-week parental leave for eligible employees and annual reimbursement/membership for Carrot Fertility.

• Time Off: 13 paid holidays annually, a holiday break between December 25th-31st, and flexible Paid Time Off (PTO).

• Professional Development: Opportunities for training and continuous learning to advance skills.

Working Hours: The standard working hours are 40 hours per week. The role is remote, offering flexibility in how and when work is completed, provided deliverables are met and collaboration with teams in various time zones is managed effectively.

📝 Enhancement Note: The salary range provided aligns with senior-level product design roles in major tech hubs. The extensive benefits package, particularly the focus on mental health and family support, reflects a company culture that prioritizes employee well-being, which is a significant draw for experienced professionals. The remote work stipend and flexible PTO further enhance the attractiveness of the total compensation package.

🎯 Team & Company Context

🏢 Company Culture

Industry: Mental Healthcare Technology / SaaS. Headway operates at the intersection of healthcare and technology, aiming to democratize access to mental health services by simplifying insurance and practice management for providers. This industry requires a high degree of trust, compliance, and user empathy.

Company Size: Series D funded, indicating a significant growth stage with established processes but still maintaining agility. The company size is likely several hundred employees, offering opportunities for impact without being lost in a massive organization.

Founded: Headway was founded to address a critical gap in mental healthcare accessibility. Their mission-driven approach is central to their culture, attracting individuals passionate about making a tangible difference.

Team Structure: The "Client Management pod" implies a team structure focused on specific user segments or product areas. As a Senior Designer, you would be a key leader within this pod, working closely with a Product Manager, Engineers, and a Data Analyst. You will also be part of a broader Product Design team, contributing to and benefiting from shared practices and a unified design system.

Methodology: Headway emphasizes an AI-first design approach, integrating AI tools into the daily workflow for rapid prototyping, iteration, and efficiency. They are data-informed, using both qualitative and quantitative insights to guide product development. The company fosters a culture of cross-functional collaboration, aiming for tight alignment between design, product, engineering, and data.

Company Website: https://headway.co/

📝 Enhancement Note: The company's mission to improve mental healthcare access is a strong cultural anchor. For operations professionals, this translates to a focus on efficiency, scalability, and user experience that directly impacts patient care. The AI-first approach signals a commitment to innovation and leveraging technology for operational advantages.

📈 Career & Growth Analysis

Operations Career Level: This role is designated as "Senior Product Designer," indicating a mid-to-senior level position. It requires a high degree of autonomy, strategic thinking, and the ability to lead design initiatives for complex product areas. The role is expected to influence product strategy and mentor junior designers.

Reporting Structure: You will report to a Design Lead or Head of Design, and work daily within a cross-functional "pod" (Product Manager, Engineers, Data Analyst) focused on Client Management. This structure allows for deep collaboration and shared ownership of outcomes.

Operations Impact: While a design role, your work on scheduling and messaging directly impacts the operational efficiency of over 75,000 providers on the Headway platform. By reducing administrative burdens, you enable providers to serve more patients, improve their practice sustainability, and ultimately drive Headway's mission forward. Accurate scheduling and clear communication are fundamental to a smooth operational flow for both providers and patients.

Growth Opportunities:

• Leadership in Design: Opportunity to lead design for a critical product area, influencing product strategy and potentially mentoring junior designers.

• AI Design Specialization: Deepen expertise in AI-first design methodologies, becoming a go-to person for AI tool integration and best practices within the design team.

• Domain Expertise: Develop deep understanding of the mental healthcare industry and the unique operational challenges faced by providers.

• Design System Evolution: Contribute significantly to the Helix design system, building a reputation for creating reusable, high-quality design patterns.

• Cross-functional Influence: Expand influence across Product, Engineering, and Data, driving user-centricity and operational efficiency across the organization.

📝 Enhancement Note: The "Senior" title, coupled with the emphasis on leading a pod and contributing to design systems and AI integration, suggests a clear path for growth into Principal Designer, Design Lead, or specialized AI design roles within Headway. The operational impact is significant, making this a role where design decisions have tangible business and user outcomes.

🌐 Work Environment

Office Type: The role is fully remote, within the United States. This offers significant flexibility for operations professionals to manage their work environment and schedule.

Office Location(s): While remote, the company headquarters are in New York, NY, and the salary range is benchmarked to this high-cost-of-living area. The company also participates in E-Verify, a standard for US-based employers.

Workspace Context:

• Remote Flexibility: The primary work environment is your home office, allowing for personalized setup and greater work-life integration.

• Digital Collaboration: All collaboration will occur digitally through video conferencing, messaging platforms, and collaborative design tools.

• Operations Tools Access: You will have access to the necessary digital tools and software, including AI prototyping tools, design software, and communication platforms, to perform your job effectively.

• Cross-functional Interaction: Regular interaction with Product Managers, Engineers, Data Analysts, and other designers, fostering a collaborative and inclusive remote working environment.

Work Schedule: While a standard 40-hour work week is expected, the remote nature of the role allows for flexibility. Operations professionals often benefit from the ability to structure their day to accommodate deep work sessions, team meetings, and personal needs, provided they maintain availability for critical cross-functional touchpoints and meet project deadlines.

📝 Enhancement Note: The fully remote nature of this position is a key aspect. For operations professionals, this means the ability to structure their day around peak productivity times and minimize commute-related stress, focusing instead on delivering high-quality design work and collaborating effectively through digital channels. The "New York" location in the listing likely serves as a salary benchmark rather than a physical requirement.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter will likely review your application and portfolio for alignment with the core requirements, focusing on your experience with complex workflows, AI tools, and cross-functional collaboration.

• Portfolio Review & Design Challenge: You will likely present your portfolio, highlighting case studies that demonstrate your systems thinking, AI integration, and impact on user workflows. A design challenge, potentially focused on a scheduling or messaging scenario, may be given.

• Cross-functional Interviews: Interviews with Product Management, Engineering, and Data teams to assess your collaboration skills, technical understanding, and approach to data-informed design.

• Hiring Manager Interview: A final interview with the hiring manager (likely Head of Design or Design Lead) to discuss your strategic thinking, leadership potential, and cultural fit.

Portfolio Review Tips:

• Highlight AI Integration: Clearly showcase how you've used AI tools in your process. For example, demonstrate how AI helped you generate initial concepts, write code snippets for prototypes, or analyze user feedback more efficiently.

• Emphasize Workflow Optimization: For each case study, clearly articulate the "before" state of the workflow, the problems encountered by users (providers), your design solutions, and the measurable improvements in efficiency, task completion, or error reduction. Use metrics where possible.

• Showcase Systems Thinking: Explain how your design decisions contribute to the overall coherence of the product and the design system. If you contributed to the Helix design system, detail your contributions.

• Tell a Story: Structure your case studies as narratives. Start with the problem, detail your process (including research, ideation, AI usage, and iteration), and conclude with the impact and learnings.

• Be Prepared for Code/Prototyping Discussions: Given the AI-first approach, be ready to discuss your prototyping methods and how you engage with code or AI-assisted code generation.

Challenge Preparation:

• Deconstruct the Problem: If given a design challenge, take time to understand the core problem, the user (provider), and the constraints.

• Think Systemically: Consider how your proposed solution fits into the broader Headway platform and impacts other workflows.

• Leverage AI Prompting: Practice using AI tools to quickly generate ideas, explore different UI approaches, or even draft initial user flows or copy.

• Focus on Edge Cases: For scheduling and messaging, the devil is in the details. Be prepared to discuss how you'd handle time zones, conflicts, notifications, and various user states.

• Articulate Your Rationale: Be clear and concise in explaining your design choices, referencing data and user insights, and how your proposed solution aligns with Headway's mission.

📝 Enhancement Note: The emphasis on AI tools suggests that candidates should be prepared to discuss their practical application in design. Portfolio case studies should not just show what was designed, but how AI was used to achieve it more effectively or efficiently. This is a key differentiator for this role.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (likely the primary tool for UI design and prototyping), potentially Sketch.

• AI Prototyping & Development Assistance: Claude Code, Cursor, MagicPatterns (explicitly mentioned as core to the workflow).

• Design Systems: Helix (Headway's internal design system).

• Collaboration & Communication: Slack, Zoom, Google Workspace.

Analytics & Reporting:

• Product Analytics: Tools like Amplitude, Mixpanel, or similar for understanding user behavior within the platform.

• Data Visualization: Tableau, Looker, or internal dashboards for presenting data insights.

CRM & Automation:

• CRM: While not directly a CRM role, understanding how providers manage their client lists and profiles within Headway is crucial (internal CRM-like functionalities).

• Integration Tools: Awareness of how different systems (e.g., Google Calendar OAuth) integrate and the design considerations thereof.

📝 Enhancement Note: The explicit mention of AI tools like Claude Code, Cursor, and MagicPatterns is critical. Candidates must be comfortable and proficient with these technologies, or demonstrate a strong ability to learn and integrate them quickly. This is a defining characteristic of Headway's design team.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A deep commitment to improving mental healthcare access and empowering providers. This translates to a focus on impact and user well-being in all operational and design decisions.

• AI-First Innovation: Embracing AI as a core tool for efficiency, rapid iteration, and enhanced design capabilities. This requires a proactive and experimental mindset.

• Data-Informed Decisions: Relying on both qualitative and quantitative data to guide product development and measure success, fostering a culture of evidence-based strategies.

• Systems & Coherence: Valuing the creation of robust, scalable systems and maintaining design consistency across the platform, essential for complex operational tools.

• Collaboration & Alignment: Strong emphasis on cross-functional teamwork, open communication, and building consensus to drive projects forward effectively.

Collaboration Style:

• Pod-Based Autonomy: Working within small, empowered cross-functional pods (PM, Eng, Data, Design) with a high degree of ownership and collaboration.

• Design System as a Shared Language: Utilizing the Helix design system as a common framework for design and development, ensuring consistency and efficiency.

• Open Feedback Culture: Encouraging constructive feedback loops among team members to continuously improve designs and processes.

• Proactive Communication: Given the remote nature, proactive and transparent communication is essential for maintaining alignment and momentum.

📝 Enhancement Note: The "AI-First" value is particularly noteworthy. It suggests that candidates who can demonstrate initiative in adopting and leveraging new technologies, especially AI, will fit well into Headway's culture. This aligns with a forward-thinking approach to operations and product development.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of State Management: Designing for intricate scheduling, availability, and messaging scenarios with numerous edge cases (time zones, conflicts, notifications) requires meticulous attention to detail and robust problem-solving skills.

• Balancing Provider Needs with Patient Access: Ensuring the tools are intuitive and efficient for providers while also facilitating seamless patient booking and communication.

• Integrating AI Seamlessly: Effectively leveraging AI tools to enhance the design process without compromising user experience or design integrity.

• Maintaining Design System Coherence: As new features are developed, ensuring they align with and extend the existing Helix design system.

• Remote Collaboration Dynamics: Navigating effective communication and collaboration within a fully remote, cross-functional team structure.

Learning & Development Opportunities:

• AI Design Mastery: Becoming a leader in AI-assisted product design through hands-on experience and continuous learning.

• Healthcare Tech Expertise: Deepening knowledge of the mental healthcare industry, its operational challenges, and regulatory landscape.

• Advanced UX/UI Craft: Refining skills in complex workflow design, interaction patterns, and visual polish for enterprise-grade SaaS applications.

• Design Leadership: Developing skills in mentoring, strategic product input, and contributing to design team best practices.

• Cross-functional Acumen: Enhancing ability to influence and collaborate with diverse teams (Product, Engineering, Data) to achieve shared objectives.

📝 Enhancement Note: The challenges presented are typical for senior roles in complex SaaS environments, particularly in healthcare. The growth opportunities are substantial, offering a chance to become an expert in AI-driven design within a mission-critical industry.

💡 Interview Preparation

Strategy Questions:

• Design Process & AI Integration: "Walk me through a complex workflow problem you solved recently. How did you approach it, what were the key challenges, and how did you leverage AI tools in your process?" (Focus on systems thinking, problem decomposition, and AI application).

• Cross-functional Collaboration: "Describe a time you had to build alignment with Product, Engineering, and Data on a challenging design decision. How did you approach communication and compromise?" (Highlight communication skills, data-informed rationale, and stakeholder management).

• Problem-Solving & Impact: "Imagine a provider is frequently missing appointments due to scheduling conflicts. How would you approach designing a solution to prevent this, and how would you measure its success?" (Demonstrate analytical thinking, user empathy, and focus on operational efficiency and measurable outcomes).

Company & Culture Questions:

• Mission Alignment: "What about Headway's mission resonates with you, and how do you see your role contributing to it?" (Show genuine interest and understanding of the company's purpose).

• AI Design Philosophy: "How do you see AI tools changing the future of product design, and what's your philosophy on integrating them into a workflow?" (Assess your forward-thinking approach and comfort with new technologies).

• Teamwork & Feedback: "How do you prefer to give and receive feedback within a design team and with cross-functional partners?" (Evaluate your collaborative spirit and openness to constructive criticism).

Portfolio Presentation Strategy:

• Lead with Impact: Start each case study by clearly stating the problem, your role, and the key outcomes or impact achieved.

• Show, Don't Just Tell: Use visuals (screenshots, flows, prototypes) to illustrate your design process and solutions. For AI tools, show examples of prompts, outputs, or how they accelerated your work.

• Explain Your "Why": For every design decision, articulate the rationale based on user research, data, or system constraints. Explain why you chose a particular approach.

• Discuss Trade-offs: Be prepared to discuss design trade-offs you made and why. This demonstrates critical thinking and an understanding of practical constraints.

• Engage with Questions: Treat the presentation as a conversation. Be ready to dive deeper into specific aspects of your work and answer detailed questions about your process and decisions.

📝 Enhancement Note: Preparing to discuss specific examples of how AI tools were used to solve design problems or accelerate workflows will be crucial. Candidates should be ready to demonstrate not just proficiency, but strategic application of these tools.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the official Headway careers page linked via Ashby.

• Tailor Your Resume: Highlight experience in complex workflow design, AI tool utilization, and cross-functional collaboration. Quantify achievements related to efficiency gains or user satisfaction where possible.

• Curate Your Portfolio: Select 2-3 strong case studies that clearly demonstrate your systems thinking, AI integration, and impact on operational efficiency. Ensure your portfolio is easily navigable and visually polished.

• Prepare Your Narrative: Practice articulating your design process, focusing on the "why" behind your decisions, your approach to complex problems, and how you leverage AI tools. Be ready to present your portfolio confidently.

• Research Headway: Understand their mission, products, and recent developments. Be prepared to discuss how your skills and values align with their culture and goals, especially their AI-first approach.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.